Phthalimide plasticizer and non-proteinaceous resin mix

ABSTRACT

This invention relates to the use of certain phthalimides as plasticizers for non-proteinaceous thermoplastic resins.

United States Patent Sears 51 Mar. 28, 1972 [54] PHTHALIMIDE PLASTICIZERAND NON-PROTEINACEOUS RESIN MIX [72] Inventor: James Kern Sears, St.Louis, Mo.

[73] Assignee: Monsanto Company, St. Louis, Mo.

[22] Filed: Jan. 18, 1971 [21] Appl. No.: 107,469

Related U.S. Application Data [63] Continuation-impart of Ser. No.704,562, Feb. 12,

[52] U.S. Cl. ..l06/l76 [51] Int. Cl. ..C08b 27/52 [58] Field of Search106/177; 260/326 R [56] References Cited UNITED STATES PATENTS 2,452,31510/1948 Morgan ..260/326 R Primary Examiner-Theodore MorrisAttorney-Neal E. Willis, J. E. Maurer and Robert E. Wexler [57] ABSTRACTThis invention relates to the use of certain phthalimides asplasticizers for non-proteinaceous thermoplastic resins.

23 Claims, No Drawings PIITI-IALIMIDE PLASTICIZER AND NON- PROTEINACEOUSRESIN MIX This application is a continuation-in-part of application Ser.

No. 704,562, filed Feb. 12, 1968.

This invention relates to new and useful thermoplastic resinouscompositions. In particular, this invention relates to new and improvedthermoplastic resinous compositions containing certain phthalimideswhichrimprove the physical properties of the starting resin.

Normally, vinyl halide polymers such as polyvinyl chloride andcopolymers thereof, which are widely employed in the plastics industry,are quite hard and brittle in nature and require the addition ofsubstantial proportions of a plasticizer to improve their workability.Since some of the plasticizer is ordinarily retained in the plasticproduct, it is desirable that it possess certain characteristics. Amongthese desirable characteristics is the ability of a plasticizer toimpart low-temperature flexibility to the product. The plasticizer mustalso be of low volatility to prevent its loss by evaporation. Otherdesirable characteristics of a plasticizer include low water absorptionand leaching. It is also desirable that the plasticizer be one whichdoes not allow the finished product be become hard and brittle andthereby easily fractured.

It is accordingly an object of this invention to provide improvednon-proteinaceous thermoplastic resinous compositions.

It is a further object of this invention to provide novel plasticcompositions comprising thermoplastic resins and certain phthalimides.

A still further object is to provide new resinous compositions havingdesirable physical properties.

Other objects and advantages of the invention will be apparent to thoseskilled in the art from the following detailed description and claims.

In accordance with this invention, it has been found that the above andstill further objects are achieved by incorporating a thermoplasticresin and certain phthalimides.

Generally speaking, about to 200 parts by weight of plasticizer can beused for each 100 parts by weight of thermoplastic resin. However, it ispreferred to use from about 20 to 100 parts by weight of plasticizer per100 parts by weight of resin.

The phthalimides of this invention are effective as plasticizers fornon-proteinaceous thermoplastic resins and rubberlike materials.Examples of non-proteinaceous materials suitable for use with thisinvention include vinyl chloride polymers or copolymers, polyvinylacetate, lower alkyl cellulose ethers such as methyl cellulose, ethylcellulose, butyl cellulose and aralkyl cellulose ethers such as benzylcellulose, cellulose esters of organic acids having two to four carbonatoms such as cellulose acetate, cellulose propionate, cellulosebutyrate, cellulose acetate-butyrate and cellulose acetatepropionate,vinyl aromatic resins such as polystyrene, rubbery polymers such as thecopolymers of butadiene with styrene or acrylonitrile and the terpolymerof acrylonitrile, butadiene and styrene, and polymers of a-monoolefinshaving two to carbon atoms such as the polymers and copolymers ofethylene, propylene, butene-l and the like. Polymers of methylmethacrylate suitable for use in the practice of this invention includehomopolymers of methyl methacrylate or copolymers with minor amounts,for example, up to 25 per cent by weight, of another ethylenicallyunsaturated monomer copolymerizable therewith, for example, acrylicacid, methacrylic acid, the one to four carbon alkyl (i.e., methyl tobutyl) esters of acrylic acid, the two to four carbon alkyl (i.e.,ethyl, propyl and butyl) esters of methacrylic acid, vinyl acetate,acrylonitrile, various amides and styrene.

This invention is particularly applicable to halogen-containing vinylresins. Thus, there may be employed resins derived from such vinylcompounds as vinyl chloride, vinyl chloroacetate, chlorostyrene,chlorobutadienes, etc. Said resins also include the copolymers of suchvinyl compounds and other ethylenically unsaturated monomerscopolymerizable therewith. Illustrative are the copolymers of a vinylhalide,

such as vinyl chloride, with other monomers such as vinylidene chloride;vinyl esters of carboxylic acids, e.g., vinyl acetate, vinyl'propionate, vinyl butyrate, vinyl benzoate; esters of unsaturated acids,e.g., alkyl acrylates such as methyl acrylate, ethyl acrylate, propylacrylate, butyl acrylate, allyl acrylate, and the corresponding estersof methacrylic acid; vinyl aromatic compounds, e.g., styreneortho-chlorostyrene, para-chlorostyrene, 2,5-dichlorostyrene,2,4-dichlorostyrene, para-ethyl styrene, vinyl naphthalene, cit-methylstyrene, dienes such as butadiene and chlorobutadiene; unsaturatedamides such as acrylic acid amide and acrylic acid anilide; unsaturatednitriles such as acrylic acid nitrile; esters of 0:,fl-unsaturatedcarboxylic acids, e.g., the methyl, ethyl, propyl, butyl, amyl, hexyl,heptyl, octyl, allyl, metallyl and phenyl esters of maleic, crotonic,itaconic and fumaric acids and the like. It should be recognized thatthe halogenated resins containing halogens other than chlorine, e.g.,bromine, fluorine and iodine, are also operable in this invention. Thehalogenated resins may contain a varying proportion of halogen,depending upon the nature of the resin and its contemplated use. Thosecopolymers in which a predominant portion, i.e., more than 50 percent byweight of the copolymer, is made from a halogen-containing vinylidenemonomer such as vinyl chloride represent a preferred class of polymersto be treated according to this invention.

The phthalimides useful as plasticizers with this invention have thegeneral formula wherein R is selected from the group consisting of alkylhaving seven to 20 carbon atoms, mixed alkyl having seven to 18 carbonatoms, cycloalkyl having seven to 18 carbon atoms, aryl having seven to10 carbon atoms, aralkyl having seven to nine carbon atoms, alkarylhaving seven to 18 carbon atoms and alkoxyalkyl having seven to 8 carbonatoms.

The alkyl and cycloalkyl radicals can be derived from many sources. Forexample, the alkyl radicals can be straight or branched chain radicalshaving up to 20 carbon atoms derived from various sources such asalcohols, including alcohols produced by the 0x0 synthesis or alcoholsobtained by catalytic hydrogenation of coconut oil, from oxidized waxesor from esterification of a carbonyl group by reaction with an olefin.Illustrative examples of alkyl radicals are heptyl, 2- ethylheptyl,2-ethylhexyl, octyl, isooctyl, 2-octyl, isononyl, dycyl, lauryl,tridecyl, tetradecyl, pentadecyl, octadecyl, crotyl, oleyl, alkylradicals derived from C to C oxo alcohols, etc. Illustrative examples ofcycloalkyl radicals are 2,4-dimethylcyclopentyl, 3,5-dimethylcyclohexyl,gem.- dimethylcyclohexyl, cyclohexylmethyl, cyclohexylpropyl,methylcyclohexylethyl, 2propylcyclohexyl, 3-dodecylcyclohexyl,cycloheptyl, 2,4-dimethylcycloheptyl, 2,3,5- trimethylcycloheptyl, etc.

Illustrative examples of aryl radicals are biphenyl, napthyl, etc.Illustrative examples of aralkyl radicals are benzyl, 4- methylbenzyl,3-phenylpropyl, phenethyl, etc. Examples of alkaryl radicals useful withthe invention include methylphenyl, butylphenyl, hexylphenyl,octylphenyl, nonylphenyl, dodecylphenyl, l-methylnaphthyl,2-methylnaphthyl, etc. I1- lustrative examples of alkoxyalkyl radicalsare ethoxyamyl, methoxyhexyl, propoxybutyl, butoxybutyl and the like.

The mixed alkyl radicals can be derived from mixtures of straight chainaliphatic alcohols having between seven and about 18 carbon atoms. Theseare represented by the alcohols marketed by Continental Oil Companyunder the trade name .Alfol 810, Alfol 1214, Alfol 1216 and Alfol 1618and alcohols marketed by Archer Daniels Midland Company under the tradename Adol 9, Adol l2, Adol 52 and Adol 63. Alfol 810 consists primarilyof 43% C alcohols and 55% C alcohols. Alfol 1214 comprises approximately55% C alcohols and 43% C alcohols. Alfol 1216 has a compositionapproximating 63% C alcohols, 24% C alcohols, C alcohols and Alfol 1618has 63% C alcohols, 30% C alcohols and 2% C alcohols. Adol 9 is amixture of straight chain fatty alcohols having the followingcomposition: 55% C alcohols, 35% C alcohols and 10% C alcohols. Adol 12consists primarily of 2% C alcohols, 90% C alcohols arid 8% C alcohols.Adol 52 has an approximate composition of 4% C alcohols, 90% C alcoholsand 6% C alcohols. Ado] 63 comprises l% C alcohols, 6% C alcohols, 30% Calcohols, 60% C alcohols and 3% C alcohols.

It is basic that blends of resins and plasticizers must be compatible toavoid obvious problems such as blooming, etc. Accordingly, theplasticizers utilized herein must be of a structure that hydrogenbonding does not take place between the plasticizer and thethermoplastic resin. Thus, the plasticizer must contain no activehydrogens and must be free of polarityinducing groups, such as hydroxylor amino groups, since such groups permit hydrogen bonding and theplasticizer would therefore be unsuitable for use in thermoplasticresins such as polyvinyl chloride. Conversely, compatibilizing groups,such as ester, ketone and halogen groups are desirable in the structureof the plasticizers disclosed herein.

The plasticizers of the present invention are readily prepared bymethods well known in the art. For example, the phthalimides may beprepared by reacting phthalic acid or phthalic anhydride with anappropriate primary amine or by reacting potassium phthalimide with analkyl halide. Each of these methods of preparing the phthalimides isfully shown and described in Beilstein, Organische Chemie 21 461-469.

The invention will be more readily understood by reference to thefollowing examples which describe the advantageous and unexpectedresults achieved by the use of the plasticizers of the present inventionin thermoplastic resins. There are, of course, many other forms of thisinvention which will become obvious to one skilled in the art, once theinvention has been fully disclosed, and it will accordingly berecognized that these examples are given for the purpose of illustrationonly, and are not to be construed as limiting the scope of thisinvention in any way.

The following testing procedures are used in evaluating the physicalproperties and efficiency of plasticizers.

Compatibility Visual inspection of the plasticized composition isemployed, incompatibility of the plasticizer with the polymer beingdemonstrated by cloudiness and exudation of the plasticizer.

Low-temperature Flexibility Low-temperature flexibility is one of themost important properties of elastomeric vinyl compositions. While manyplasticizers will produce flexible compositions at room temperature, theflexibility of these compositions at low temperature may varyconsiderably, i.e., plasticized polyvinyl chloride compositions that areflexible at room temperature often become very brittle and useless atlower temperatures. Low-temperature flexibility tests herein employedare according to the Clash-Berg Method. This method determines thetorsional flexibility of a plastic at various temperatures. Thetemperature at which the vinyl composition exhibits an arbitrarilyestablished minimum flexibility is defined as the low-temperatureflexibility of the composition. This value may also be defined as thelower temperature limit of the plasticized compositions usefulness as anelastomer.

Kerosene Extraction Resistance to kerosene is measured as follows: A2-inch diameter 40-mil disc is suspended in a 50- C. oven for a 3-hourconditioning period to eliminate water, then cooled and weighed. Theconditioned sample is then immersed in 400 ml. of kerosene for a periodof 24 hours at 23 C. The sample is then removed from kerosene, blotteddry and suspended in a force draft 80 C. oven for 4 hours. The sample isthen cooled and weighed 'lh'e percent loss in weight is reported as thekerosene-extraction value.

Water Resistance The amount of water absorption and the amount of waterleaching that take place when the plasticized composition is immersed indistilled water for 24 hours is determined.

Hardness A standard instrument made by Shore Instrument Company is usedfor this detennination and expresses the hardness in units from one to100. The hardness of the composition is judged by its resistance to thepenetration of a standard needle applied to the composition under astandard load for a standard length of time.

The following examples illustrate the advantageous and unexpectedresults which are achieved by the use of the plasticizers of the'presentinvention in thermoplastic resinous compositions but it is not intendedthat this invention be limited by or to such examples.

EXAMPLE 1 One hundred parts by weight of polyvinyl chloride and 40 partsby weight of N-isooctyl phthalimide are mixed on a rolling mill to ahomogeneous blend. During the milling, substantially no fuming ordiscoloration is observed. Testing of the molded sheet forlow-temperature flexiblity, according to the procedure described above,gives a value of 20.9' C., which value denotes good low-temperatureproperties. Tests of the water resistance of the plasticized materialshow a loss of soluble matter of 0.30 percent and a water absorptionvalue of 0.46 percent. A Shore hardness value of 71 is obtained on thiscomposition. The plasticized material has a kerosene extraction value of5.6 percent.

EXAMPLE 2 Following the procedure of Example 1, the N-isooctylphthalimide plasticizer is replaced with 40 parts by weight of thefollowing plasticizers:

N-heptyl phthalimide N-octyl phthalimide N-nonyl phthalimide N-decylphthalimide N-dodecyl phthalimide N-tridecyl phthalimide N-octadecylphthalimide N-ethoxyamyl phthalimide N-methoxyhexyl phthalimideN-butoxypropyl phthalimide N-butoxybutyl phthalimide The plasticizedresin compositions exhibit physical properties similar to thosedemonstrated in Example 1.

Similar results are obtained when theabove phthalimides are compared atlevels of 20, 30, 60, and 75 phr. (parts of plasticizer per hundredparts by weight of resin).

The substitution of other vinyl halide-containing resins for thepolyvinyl chloride used in the examples, also results in effectiveplasticization. Similar improved compositions are obtained when thepolyvinyl chloride is replaced by an equivalent amount of a copolymer ofparts of vinyl chloride and 5 parts of vinyl acetate, a copolymer of 90parts of vinyl chloride and 10 parts of vinylidene chloride and acopolymer of 70 parts of vinyl chloride and 30 parts of diethylmaleate.

EXAMPLE 3 Individual plasticized compositions are prepared in accordancewith the procedure of Example 1 wherein the polyvinyl chloride isreplaced in each instance by parts by weight of polymethyl acrylate, 100parts of weight of polymethyl methacrylate, 100 parts by weight of acopolymer of 98 parts of methyl methacrylate and 2 parts of methacrylicacid, 100 parts by weight of a copolymer of 80 parts of methylmethacrylate and 20 parts of glycidyl methacrylate, and 100 parts byweight of a copolymer of 70 parts of methyl methacrylate and 30 parts ofmethyl acrylate. In each instance, the results parallel those obtainedin the first example.

EXAMPLE 4 Samples of cellulose acetate, cellulose propionate, celluloseacetate butyrate, cellulose nitrate, methyl cellulose, ethyl cellulose,butyl cellulose and benzyl cellulose are mixed on a rolling mill to ahomogeneous blend with 20 parts by weight of N-isooctyl phthalimide per100 parts by weight of each thermoplastic resin. The resultant productsare pressed into films and are found to be more flexible than filmsobtained from the thermoplastic resins in the absence of theplasticizer.

EXAMPLE 5 The procedure of Example 1 is repeated except thatthepolyvinyl chloride is replaced by 100 parts by weight of individualresins, namely, polyethylene, polypropylene, polyvi-' nyl acetate,polystyrene, a copolymer of 40 parts of styrene and 60 parts ofacrylonitrile and a copolymer of 70 parts of styrene and 30 parts ofacrylonitrile. In each instance, the plasticized resin compositionsexhibit physical properties comparable to those demonstrated in theprevious examples.

The phthalimides of the present invention may be employed as the soleplasticizer in resin compositions or may be used in combination withother known conventional plasticizers or softening agents commonlyemployed with such resins. Illustrative of the latter plasticizers arediethyl phthalate, dibutylphthalate, di-Z-ethylhexylphthalate, dibutylsebacate, triethyl phosphate, trioctyl phosphate and methyl phthalylethylglycolate.

For many purposes, it may be desirable to blend other conventionaladditives with the plasticized thermoplastic resinous compositions ofthe present invention. Illustrative of such additives are fillers, dyes,pigments, heat and light stabilizers, lubricants and the like. it willbe apparent that compositions containing such other additives are withinthe scope of this invention.

While this invention has been described with respect to certainembodiments, it is not so limited, and it should be understood thatvariations and modifications thereof may be made which are obvious tothose skilled in the art without departing from the spirit or scopeofthe invention.

The embodiments of the invention in which an exclusive property orprivilege is claimed are defined as follows:

1. A non-proteinaceous composition of matter comprising a thermoplasticresin and a plasticizer therefor having the general formula wherein R isselected from the group consisting of a hydrocarbon alkyl having sevento 20 carbon atoms, mixed alkyl having seven to 18 carbon atoms,cycloalkyl having seven to 18 carbons atoms, aryl having seven to carbonatoms, aralkyl having seven to nine carbon atoms, alkaryl having sevento 18 carbon atoms and alkoxyalkyl having seven to 8 carbon atoms andalkoxyalkyl having seven to 8 carbon atoms, wherein said plasticizer ispresent in plasticizing amounts of from about five to about 200 parts byweight per 100 parts by weight of said resin.

2. A composition as defined in claim 1 wherein R is alkyl having sevento 12 carbon atoms.

3. A composition as defined in claim 1 wherein said compound isN-isooctyl phthalimide.

4. A composition as defined in claim 1 wherein said compound is presentin amounts of from about 20 to about 100 parts by weight per 100 partsby weight of said thermoplastic resin.

5. A composition as defined in claim 1 wherein said thermoplastic resinis a vinyl halide polymer selected from the group consisting ofpolymerized vinyl halide monomers and copolymers of such monomers withan ethylenically unsaturated monomer, at least 50 percent of the monomerunits of said copolymers being vinyl halide units.

6. A composition as defined in claim 1 wherein said thermoplastic resinis a vinyl halide polymer selected from the group consisting ofpolymerized vinyl halide monomers and copolymers of such monomers withan ethylenically unsaturated monomer, at least 50 percent of the monomerunits of said copolymers being vinyl halide units and R is alkyl havingfour to 12 carbon atoms.

7. A composition as defined in claim 1 wherein said thermoplastic resinis a vinyl halide polymer selected from the group consisting ofpolymerized vinyl halide monomers and copolymers of such monomers withan ethylenically unsaturated monomer, at least 50 percent of the monomerunits of said copolymers being vinyl halide units and said compound isN-isooctyl phthalimide.

8. A composition as defined in claim 1 wherein said thermoplastic resinis polyvinyl chloride and said compound is N- isooctyl phthalimide.

9. A composition as defined in claim 1 wherein said thermoplastic resinis a polymer of an a-monoolefin having two to 10 carbon atoms.

10. A composition as defined in claim 1 wherein said thermoplastic resinis a polymer of an a-monoolefin having two to 10 carbon atoms and R isalkyl having four to 12 carbon atoms.

11. A composition as defined in claim 1 wherein said thermoplastic resinis a cellulose ester of an organic acid having a two to four carbonatoms.

12. A composition as defined in claim 1 wherein said thermoplastic resinis a cellulose ester of an organic acid having two to four carbon atomsand R is alkyl having seven to 12 carbon atoms.

13. A composition as defined in claim 1 wherein said thermoplastic resinis a cellulose ester of an organic acid having two to four carbon atomsand said compound is N-isooctyl phthalimide.

14. A composition as defined in claim 1 wherein said thermoplastic resinis a cellulose ether selected from the group consisting of lower alkylcellulose ethers and aralkyl cellulose ethers.

15. A composition as defined in claim 14 wherein said cellulose ether isethyl cellulose.

16. A composition as defined in claim 14 wherein said cellulose ether isbutyl cellulose.

17. A composition as defined in claim 14 wherein said cellulose ether isbenzyl cellulose.

18. A composition as defined in claim 1 wherein said thermoplastic resinis a cellulose ether selected from the group consisting of lower alkylcellulose ethers and aralkyl cellulose ethers and R is alkyl havingseven to 12 carbon atoms.

19. A composition as defined in claim 1 wherein said thermoplastic resinis a polymer of methyl methacrylate selected from the group consistingof homopolymers of methyl methacrylate and copolymers of methylmethacrylate containing at least 75 percent methyl methacrylate and upto 25 percent of an ethylenically unsaturated monomer copolymerizabletherewith.

20. A composition as defined in claim 1 wherein said thermoplastic resinis a polymer of methyl methacrylate selected from the group consistingof homopolymers of methyl methacrylate and copolymers of methylmethacrylate containing at least 75 percent methyl methacrylate and upto 25 percent of an ethylenically unsaturated monomer copolymerizabletherewith and R is alkyl having seven to 12 carbon atoms.

21. A composition as defined in claim 1 wherein said thermoplastic resinis a polymer of methyl methacrylate selected from the group consistingof homopolymers of methyl methacrylate and copolymers of methylmethacrylate contain- 7 8 ing at least 75 percent methyl methacrylateand up to 25 per- 23. A composition as defined in claim 1 wherein saidthercent of an ethylenically unsaturated monomer copolymerizamoplasticresin is a op lymer f m ou 4 to about 70 ble therewith and said compoundis N-isooctyl phthalimide. Parts Of yr ne and r about 3 o abo 60 partsof 22. A composition as defined in claim 1 wherein said ther- 5acrylonitrilcmoplastic resin is polymethyl methacrylate.

use 101029 ban

2. A composition as defined in claim 1 wherein R is alkyl having sevento 12 carbon atoms.
 3. A composition as defined in claim 1 wherein saidcompound is N-isooctyl phthalimide.
 4. A composition as defined in claim1 wherein said compound is present in amounts of from about 20 to about100 parts by weight per 100 parts by weight of said thermoplastic resin.5. A composition as defined in claim 1 wherein said thermoplastic resinis a vinyl halide polymer selected from the group consisting ofpolymerized vinyl halide monomers and copolymers of such monomers withan ethylenically unsaturated monomer, at least 50 percent of the monomerunits of said copolymers being vinyl halide units.
 6. A composition asdefined in claim 1 wherein said thermoplastic resin is a vinyl halidepolymer selected from the group consisting of polymerized vinyl halidemonomers and copolymers of such monomers with an ethylenicallyunsaturated monomer, at least 50 percent of the monomer units of saidcopolymers being vinyl halide units and R is alkyl having four to 12carbon atoms.
 7. A composition as defined in claim 1 wherein saidthermoplastic resin is a vinyl halide polymer selected from the groupconsisting of polymerized vinyl halide monomers and copolymers of suchmonomers with an ethylenically unsaturated monomer, at least 50 percentof the monomer units of said copolymers being vinyl halide units andsaid compound is N-isooctyl phthalimide.
 8. A composition as defined inclaim 1 wherein said thermoplastic resin is polyvinyl chloride and saidcompound is N-isooctyl phthalimide.
 9. A composition as defined in claim1 wherein said thermoplastic resin is a polymer of an Alpha -monoolefinhaving two to 10 carbon atoms.
 10. A composition as defined in claim 1wherein said thermoplastic resin is a polymer of an Alpha -monoolefinhaving two to 10 carbon atoms and R is alkyl having four to 12 carbonatoms.
 11. A composition as defined in claim 1 wherein saidthermoplastic resin is a cellulose ester of an organic acid having twoto four carbon atoms.
 12. A composition as defined in claim 1 whereinsaid thermoplastic resin is a cellulose ester of an organic acid havingtwo to four carbon atoms and R is alkyl having seven to 12 carbon atoms.13. A composition as defined in claim 1 wherein said thermoplastic resinis a cellulose ester of an organic acid having two to four carbon atomsand said compound is N-isooctyl phthalimide.
 14. A composition asdefined in claim 1 wherein said thermoplastic resin is a cellulose etherselected from the group consisting of lower alkyl cellulose ethers andaralkyl cellulose ethers.
 15. A composition as defined in claim 14wherein said cellulose ether is ethyl cellulose.
 16. A composition asdefined in claim 14 wherein said cellulose ether is butyl cellulose. 17.A composition as defined in claim 14 wherein said cellulose ether isbenzyl cellulose.
 18. A composition as defined in claim 1 wherein saidthermoplastic resin is a cellulose ether selected from the groupconsisting of lower alkyl cellulose ethers and aralkyl cellulose ethersand R is alkyl having seven to 12 carbon atoms.
 19. A composition asdefined in claim 1 wherein said thermoplastic resin is a polymer ofmethyl methacrylate selected from the group consisting of homoPolymersof methyl methacrylate and copolymers of methyl methacrylate containingat least 75 percent methyl methacrylate and up to 25 percent of anethylenically unsaturated monomer copolymerizable therewith.
 20. Acomposition as defined in claim 1 wherein said thermoplastic resin is apolymer of methyl methacrylate selected from the group consisting ofhomopolymers of methyl methacrylate and copolymers of methylmethacrylate containing at least 75 percent methyl methacrylate and upto 25 percent of an ethylenically unsaturated monomer copolymerizabletherewith and R is alkyl having seven to 12 carbon atoms.
 21. Acomposition as defined in claim 1 wherein said thermoplastic resin is apolymer of methyl methacrylate selected from the group consisting ofhomopolymers of methyl methacrylate and copolymers of methylmethacrylate containing at least 75 percent methyl methacrylate and upto 25 percent of an ethylenically unsaturated monomer copolymerizabletherewith and said compound is N-isooctyl phthalimide.
 22. A compositionas defined in claim 1 wherein said thermoplastic resin is polymethylmethacrylate.
 23. A composition as defined in claim 1 wherein saidthermoplastic resin is a copolymer of from about 40 to about 70 parts ofstyrene and from about 30 to about 60 parts of acrylonitrile.